The Devil He Knows
by PrettyGirlWonder
Summary: Forming an alliance with the King of Hell comes with its fair share of complications...and benefits.


Castiel was disgusted with himself.

This entire endeavor was pointless. Crowley's scheming would serve no purpose other than to get Castiel killed, and quite possibly, the Winchesters as well. Castiel was no fool. He knew, somewhere in the recesses of his mind, that making deals with demons never ended well, and Castiel wasn't bargaining his own soul, but the souls of millions.

On the other hand, the whole world would go up in flames if he didn't stop Raphael. In every sense, Castiel was damned if he did, damned if he didn't.

That still didn't justify the way Crowley was pressing hot kissing bites along the nape of Castiel's neck. Or the fact that Castiel was desperately enjoying it.

Crowley had insisted on a kiss to seal their "deal." Castiel had refused, point-blank, at least at first. He wasn't trading his soul and he had no interest in sealing himself into a deal that he might or might not want out of in the near future. But Crowley had insisted. Fervently. Had pressed himself against Castiel's front, pulling him lightly by his messy blue tie and tugging him down into an open-mouthed kiss. Castiel had struggled and then, suddenly, had stopped. Crowley tasted of sulfur and whiskey and mint and the flavor left Castiel lightheaded. Crowley's tongue pushed into Castiel's mouth angrily, forcefully, without finesse or regard for Castiel's discomfort. The demon growled, half pleasure half victory and gathered the front of Castiel's overcoat in his fists, tugging him closer. Crowley was smaller than Castiel but he maneuvered him expertly, slamming him against the wall of the filthy torture lab Crowley had been using to interrogate alphas. Castiel shuddered as Crowley moved his mouth down to Castiel's neck, biting at the smooth, pale skin.

"I have to say, Sparkles," Crowley murmured throatily, kissing Castiel's ear before nipping at it, "you don't taste half as pure as I'd imagined."

"You've imagined this?" Castiel rasped, fists clenching and unclenching at his sides as Crowley pulled his white shirt open and slid a hot hand against his bare skin. The touch was all wrong but Castiel's body responded anyway. He could feel his steadily growing erection pressing the zipper of his pants painfully.

"What? Deflowering Dean Winchester's pet angel? How could I not?" Crowley rocked his hips forward, providing much needed friction to Castiel's groin. Castiel groaned and finally brought his hands up to tug at Crowley's belt buckle. Crowley chuckled, a low, filthy sound.

"Eager, aren't we?"

"Shut up." Castiel undid Crowley's belt and had his pants unbuttoned and unzipped in seconds. He shoved his hand below the elastic waistband of Crowley's silk boxers and fisted his cock. Crowley grunted and jerked his hips forward into Castiel's hand, drops of pre-come leaking onto Castiel's skin.

"Fuck, Cas, you're better at this than I thought you'd be," Crowley groaned, as Castiel swiped his thumb over the head of Crowley's dick.

"I'm an angel, you ass," Castiel growled, grabbing Crowley's shoulders and spinning them so that the demon was now pressed to the wall, "I know every way imaginable to undo you."

Castiel pulled Crowley's pants to the ground, exposing his rigid, flushed cock. For a small man, Crowley was surprisingly well-endowed. Castiel wrapped his hand around the demon's dick once more, but Crowley stopped him.

"I have something else in mind, Sparkles," he said, his eyes glinting with mischief. He snapped once and Castiel's pants, which had become uncomfortably tight with the pressure of his erection, slid to his ankles. Castiel shrugged off his overcoat and suit jacket, but left his shirt, which was open and baring his chest, and his tie on. Crowley grinned.

"Better. Much better." He snapped again and the rest of Crowley's clothes disappeared. "Now then. Shall we get you ready?"

He extended his hand, revealing a small bottle of lube. Castiel stared unblinkingly at the bottle for a moment and then smiled.

"You didn't really think I'd let you penetrate me, Crowley?"

Crowley frowned, pushing his hips against Castiel's, earning himself a low groan from the angel as their cocks slid together, slicked with pre-come. "I think you're forgetting, Castiel. You're the bottom in this relationship."

Castiel did not respond. Instead he gripped Crowley's hips, locking him in place and rutting into him, cocks rubbing and sliding together, filling the air with angry, heated moans. Castiel dug his fingers in the flesh of Crowley's ass, pulling him forward and pushing their mouths into another fierce kiss, all tongues and teeth. Crowley clawed at Castiel's bare chest, dropping the bottle of lube at the angel's feet. Castiel gripped Crowley's shoulders, spun him around and dipped to retrieve the lube.

"I think," Castiel spoke directly in Crowley's ear, raising the demons arms to plant his palms on the wall, "it's time we renegotiate the terms of our 'relationship.'"

Castiel spread the cool lube on his hand and trailed his other hand down Crowley's back in an almost tender caress. He paused on his lower back, just above the demon's ass and waited. Crowley half-whimpered and stuck his ass out slightly. Castiel let out a low huff of air, which Crowley recognized as impatience, and he raised his ass higher.

"Spread." It was only one word, in that impossible gravel that was Castiel's voice and it sent Crowley spiraling almost too close to the sun. He placed his hands on either side of his ass and spread his cheeks, exposing his tight, puckered hole.

There was no warning, no sound and then suddenly, Castiel was thrusting two lube-slick fingers into Crowley. He didn't wait for a response or for Crowley to adjust, simply pumped his fingers in deep and pulled them back out before adding a third finger and repeating the process. Crowley grunted with each thrust, the pain melding with pleasure and sending sparks along his veins. He was close already and if the damned angel didn't hurry up he was going to come without even a hand on his dick.

"Cas," Crowley whined. "Enough with the foreplay, Sparkles. Just fuck me."

Castiel lubed up his cock, wincing at the heat from his own hand. He pulled Crowley's ass towards himself, digging his fingers into the demon's hips. He hovered the head of his cock just outside of Crowley's wet hole, hesitating for the fraction of a moment. This was wrong, in every sense of the word. It was one thing to make deals with the King of Hell. It was an entirely different thing to have sexual relations with him against the wall of a torture chamber for monsters. Perhaps it was a testament to how far Castiel had fallen, but in that moment, with Crowley whimpering for the angel's cock, and Castiel straining, aching to close the distance between them, he simply didn't care.

He thrust his dick into Crowley hard, not bothering to take it slow or ease himself in. He pushed his cock in to the hilt and ground his hips in place. Crowley was panting and growling for more, clearly not bothered by Castiel's roughness. Castiel pulled out and thrust back in, changing his angle and pressing into Crowley's prostate with the tip of his dick. The demon gasped out Castiel's name, both curse and praise and fucked himself back on the angel's dick. With one hand, Castiel stilled Crowley, stripping him of his ability to move. Castiel began to fuck into Crowley's ass, setting a vicious, desperate pace, eliciting more furious cursing and begging from the demon king. Castiel's fingers dug deeper into Crowley's hips and he thrust his hips forward, again and again and again, feeling his orgasm build low in his spine. He pressed two fingers to Crowley's back and said, "You may touch yourself now." Crowley fisted his leaking cock and stroked himself frantically, trying to match Castiel's thrusts. But the angel's hips had begun to stutter and he was losing his rhythm as he raced closer and closer to his release.

Crowley thrust his ass back against Castiel's dick and clenched around him, and the angel let out a strangled cry and lights flashed in front of his eyes as he came, hard and hot, into Crowley's ass. He fucked into Crowley, riding out his orgasm and reached around him to take the demon's still hard cock in his hand. He stroked him fast and hard, grunting slightly still from the aftershocks of his own release, but keeping his dick buried in the demon's ass until finally with a low moan, Crowley came, painting the wall with his release.

Panting, his forehead lightly sheened with sweat, Castiel pulled out of Crowley. He stumbled backwards a few steps, fingers trembling as he buttoned up his shirt. He smoothed his palms down his chest and in the blink of an eye, was redressed and clean. Crowley had straightened up and clothed himself as well, adjusting his suit and watching Castiel intently.

"Pleasure doing business with you, Castiel," the demon murmured, smirking lasciviously. Castiel frowned.

"This was a one-time occurrence, Crowley. I will not make it a habit."

"Of course not, darling," Crowley cooed, stepping towards Castiel. "But I'm available anytime if you change your mind."

Castiel turned away, eager to be gone from the room and from Crowley's leering presence. The sooner he left, the sooner he could put what had just happened out of his mind.

"Say hello to those boys for me," Crowley called, his voice a subtle jeer. "Give Dean a big kiss for me."

Castiel groaned inwardly. Crowley was not going to let him forget. Ever.


End file.
